N,N,N',N'-Tetramethylethylenediamine → HCID 516472, 화합물

HRID 2215673노트

반응식

HRID 2215673 반응식
C([Li])CCC.CCCCCC.CN(CCN(C)C)C.[CH3:20][C:21]1[S:25][C:24]2[C:26](=O)[CH2:27][CH2:28][C:23]=2[CH:22]=1.[CH2:30]([N:32]1[C:41]2[C:36](=[CH:37][C:38]([CH:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=2)[C:35](=[O:45])C=C1C1OC=CC=1)[CH3:31]>C1COCC1.[Cl-].[NH4+]>[CH2:30]([N:32]1[C:41]2[C:36](=[CH:37][C:38]([CH:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=2)[C:35](=[O:45])[C:27]2[CH2:28][C:23]3[CH:22]=[C:21]([CH3:20])[S:25][C:24]=3[C:26]1=2)[CH3:31]

참가 물질

8

반응물 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 516434HCID 516434, 화합물HCID 12416658HCID 12416658, 화합물HCID 178418339Butyllithium

생성물 1

HCID 516472HCID 516472, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 25517Ammonium Chloride용매

실험 절차

To a 1.53M solution of n-butyl lithium in hexane (0.47 mL, 0.72 mmol) were added under argon atmosphere TMEDA (0.11 mL, 0.72 mmol) at room temperature and then 2-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (0.11 g, 0.72 mmol) in anhydrous THF dropwise with ice cooling and stirring. The reaction mixture was stirred at room temperature for 1 hour and ice-cooled again. To this was added dropwise a solution of 1-ethyl-6-isopropylisatoic anhydride (Example 6, step 1) (0.11 g, 0.48 mmol) in anhydrous THF. The reaction mixture was stirred at room temperature for 2 hours and diluted with saturated aqueous solution of ammonium chloride. The organic layer was concentrated to dryness and the residue was dissolved in ethyl acetate. This solution was washed with saturated sodium chloride solution, dried with sodium sulfate and evaporated again. The residue was subjected to silica gel-chromatography (chloroform: acetone=9:1) and crystallization from diethyl ether to give the title compound. 1H-NMR (CDCl3) δ 1.33 (6H, d, CH(CH3)2), 1.58 (3H, t, CH2CH3), 2.64 (3H, s, CH3), 3.10 (1H, septet, CH), 3,78 (2H, s, H-4), 4,49 (2H, q, NCH2), 6.97 (1H, s, H-3), 7.49 (1H, d, H-9), 7.56 (1H, dd, H-8), 8.45 (1H, d, H-6)

후처리

  1. temperatureice-cooled again
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours
  3. concentrationThe organic layer was concentrated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThis solution was washed with saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. customevaporated again
  8. customThe residue was subjected to silica gel-chromatography (chloroform: acetone=9:1) and crystallization from diethyl ether

출처 및 근거

ORD 기록
ord-abc130b95ee24d2c8322f1dbdb04d591
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109338B2

반응 노트

불러오는 중…